Single male 45, Greek newbie: which islands?

Traveling to Greece late Aug/Sept and need some tips on reasonable but stylish (I enjoy art and design) small places to stay, good tavernas and laid back bars where you can enjoy meeting people (i.e. not honeymooners or any mecca for twenty something ravers), a place to read and get a sense of local cuisine, culture, art etc. Anyone think they might know something that could fit? Maybe someone who has been in a similar position and found the best way to experience their travels. I find this age the most difficult to travel by yourself - getting a bit self-conscious.